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The Summit Series: Day Two

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As much as this four-day summit may seem like the ideal vacation and escape from the demands of the office, for an entrepreneur, the clock never stops ticking. Business must go on. So as we sit down to a breakfast of sweet papaya, French toast and yogurt, the BlackBerries are out in full force. We might be thousands of miles away from the office in L.A. or their employees in New York City, but they're somehow still connected, and consulting the BlackBerry is one habit hard to break away from.

Shoe Drop
While some choose to do work in their rooms or enjoy the resort, more than 20 of us have chosen to spend our morning supporting the cause of one of the entrepreneurs, Blake Mycoskie (you might have seen him on "The Amazing Race"), and we set out on a 45 minute drive north of Cancun.

We will be experiencing firsthand the spirit behind Blake's business, TOMS Shoes. After traveling in Argentina and noticing the children who were too poverty stricken to afford even the basics, Blake started TOMS Shoes in 2006 and has donated a pair of shoes to a child in need for every shoe purchased ever since ("one for one" giving). To keep that mission alive, community events like the one we will be participating in allow supporters a chance to meet the children that TOMS Shoes are impacting. As we near our destination, the BlackBerries are finally packed away and the outside world disappears as we focus on the task at hand.

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And as we enter the lot filled with more than 500 children in need of shoes, suddenly this group of entrepreneurs, including Summer Rayne Oakes, an eco-model as well as a partner in SJR, a strategic consulting and brand management firm, Graham Hill, founder of Treehugger, an environmentally focused web site that focuses on sustainability and Scott Harrison, founder of Charity: Water, a non-profit aimed to bring clean water to people in developing nations by building and rehabilitating freshwater wells, are all united. Suddenly we are given the chance to impact the lives of the local families and contribute to a greater cause. It felt good. Later on, Blake will admit that he is faced with the overwhelming awareness of the world's shortage of adequate shoes and that, even while helping children in Mexico, his thoughts drift to those in Ethiopia who are facing debilitating difficulties due to their bare feet.

We have crates of shoes and lots of feet to fit and we immediately split up into four groups for efficiency. My group's first feet belong to a family of three children. Five minutes later, they're all smiles as they leave sporting their new TOMS shoes. The gratification is immediate, and I wonder why I don't do more charity work. This is what gives meaning to life, this is what will make tomorrow different from yesterday, and this is what leaves me with a feeling at the end of the day that it was one well spent.

Returning in the shuttle, we enter into a conversation about interns, the challenge of having to fork out $125,000 per year to hire a CEO and the logistics of running a business. It's back to business--but the nice thing is that, for this moment, their entrepreneurial path doesn't feel so solo and they are eager to learn from each other.

Fireside Chat with Tim Ferriss
The poolside and surrounding areas had been full of guys talking shop long-distance on their cell phones and punching away at their BlackBerries.It's clear that they could use some advice from Tim Ferriss, master at disappearing at regular intervals while letting his business run seamlessly--without him.Outlined in his wildly popular book, The 4-Hour Workweek, Tim has made the ultimate entrepreneur's dream his own reality by outsourcing busywork, delegating responsibility and releasing control. Among Tim's varied hobbies of tango dancing, scuba diving, kickboxing, acting and skiing all over the world, it is indeed a rare opportunity to catch an hour of his time, and we all have something to learn.

In a Q&A discussion-type format, Tim advises his fellow entrepreneurs how he has gone about cutting back on time-consuming tasks such as e-mails and phone calls in order to pursue his own interests, love what he does, live in the present and redistribute his retirement into "mini-retirements" enjoyed throughout his life instead of saved up at the end.Tim seems to have started out with the idea that anything is possible, and he went about finding a way to make it happen--and, as a result, he has made it happen for others.

One anonymous entrepreneur admitted that, thanks to the strategies described in Tim's book, he is able to work remotely from Mexico, undetected, without people in the office back in the States even realizing that he is away.Definitely, being an entrepreneur can easily become an all-consuming venture, one in which the line between personal time and work time becomes blurred and the business begins to own the person rather than the other way around.This was easily evident among several in the audience who gave a skeptical glance when Tim suggested limiting checking their e-mail to two times a day and others who, glued to their BlackBerries, were consumed with more pressing matters. But I think that one of Tim's key concepts made some people stop and think: at the point between relaxation and productivity, little is accomplished.

Dinner and Clubbing
While the resort has treated us well, these entrepreneurs are true to their nature and set out to explore beyond the walls. We are heading out for a night on the town in Playa del Carmen, and while the evening is young, the day has been a busy one. At dinner, I sit next to Kamo Asatryan. He was lucky to secure VC funding for his 9-month-old startup, LOLapps, a provider of distributed social applications, shortly before the economy crashed and money became scarce. So business is doing well, they're adequately financed to keep growing the company and they plan to start building application-building software for other social networking sites in the future. Kamo realized that college wasn't for him a couple of years into it--he couldn't muster the motivation when he just wasn't interested and exchanged books for real-life experience.

Heading out of the restaurant, I meet Justin Rosenstein, an engineering manager at Facebook. Justin is on the brink of change in his life because just two days ago, Dustin Moskowitz, Facebook co-founder, and he quit Facebook to start their own business. Fair enough, since Dustin convinced Justin a year and a half before to leave Google to come on board. He doesn't offer many details regarding the new business venture other than it will involve open source software but, if the success of Facebook is any indication, it's sure to please. He does reveal that they want to be able to work anywhere--probably just because they can--and might even head to New Zealand to enjoy life while working on their startup. I attempt to give him my business card as we leave the restaurant, as I want him to keep me posted on the progress. He declines, saying that he would just lose it, but suggests befriending him on Facebook. I suppose that when you're immersed in an online world, business cards do become quite antiquated.

Waiting for the rest of the group outside of the restaurant, I start talking to Duke Chung, co-founder of Parature, an on-demand customer service software. Duke received his first copy of Entrepreneur at the age of 12. His father had always wanted to start a business himself but, as consolation for the fact that he hadn't, he inspired his son with a dream. Duke became an entrepreneur, and he still has the magazine to this day. It's nice to know that Entrepreneur had a small role in this entrepreneur's big achievements.

Walking to the club, a local attempts to lure us in with "goodies." I'll leave it to the imagination what exactly he meant by that. I wasn't about to stop to find out.

As dinner transitions into clubbing, we enter a different scene. Here, we are roped off in our special VIP section. It takes some encouraging from certain members of the group, but, before long, the '80's music lures us to hit the dance floor, joining young, old, locals, tourists and even a bride. Shot girls pass with a blue liquid that looks suspicious. Yes, this is more like the Mexico I know from one college spring break spent in Cancun. Good to see that some things don't change.

This is the time to let loose--and they do. We dominate the dance floor and go nonstop for hours. For a group in which men heavily outweigh women--there are only a handful of us compared to dozens of them--I have to admire that they're dancing at all.

Legs tired, feet aching, I go in search of a chair. Joel Holland, founder of Footage Firm, a provider of stock footage, stops to talk. I am honored to learn from him that I'm one of the only reporters invited to cover the event from the inside. And it is only then that I fully realize the exclusive pass that I have been given. I have been granted special access to this dynamic group of individuals--a group of individuals that, judging by the voices outside my room, are just stumbling home in the wee hours of the morning.

Work hard, play hard.

More from the Summit Series:
Day One
Day Two
Day Three
Day Four

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